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Synfacts 2010(4): 0448-0448  
DOI: 10.1055/s-0029-1219476
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Hydrophosphonylation of Aldehydes

Contributor(s): Mark Lautens, Jane Panteleev
K. Suyama, Y. Sakai, K. Matsumoto, B. Saito, T. Katsuki*
Kyushu University, Fukuoka, Japan
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Publikationsdatum:
22. März 2010 (online)

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Significance

Chiral α-hydroxy phosphonates are useful synthetic building blocks. Although their synthesis through asymmetric hydrophosphonylation of aldehydes has been examined previously (see Review below), the reactivity of the Lewis acid catalyzed reaction is low and high enantioselectivity is difficult to attain through base-mediated protocols. The authors report a method utilizing both an aluminum-salalen catalyst and an inorganic base promoter.

Review: P. Merino, E. Marques-Lopez, R. P. ­Herrera Adv. Synth. Catal. 2008, 350, 1195-1208.